Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,6-Dichloro-4-fluoroaniline | HCID 2774008 | — |
| Reactant | 4-Azidopyridine-3-carbaldehyde | HCID 86697037 | — |
| Catalyst | Titanium Tetrachloride | HCID 24193 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178514512 | HCID 178514512 | 99.8% |
Reaction Steps
Titanium tetrachloride (1M, 4.0 mL, 4.15 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (1.0 g, 6.75 mmol), 2,6-dichloro-4-fluorophenylamine (1.22 g, 6.75 mmol) and triethylamine (2.8 mL, 20.3 mmol) in DCM (24 mL), under nitrogen. The reaction was stirred for 30 minutes at 0° C., warmed to room temperature, stirred for an additional 2 h, and concentrated under reduced pressure. The residue was dissolved in toluene and filtered though a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid (2.09 g, quant.). This crude material was employed in the next step without further purification or analysis.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09309240B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-95e5fc1900274ec280eaa8e0f08f5c1a |
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| Source note | uspto-grants-2016_04 |
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